An optically active phosphine ligand having an asymmetric center on a phosphorous atom plays an important role in a catalytically asymmetric synthesis reaction using a transition metal complex. A 1,2-bis(dialkylphosphino)benzene derivative has been suggested as an optically active phosphine ligand having an asymmetric center on a phosphorous atom in Patent Literature 1.
In Patent Literature 2, a 2,3-bis(dialkylphosphino)pyrazine derivative has been suggested. This pyrazine derivative is characterized in that its electron-withdrawing property, which is derived from a pyrazine skeleton, is very high and that because of this the electron density of the phosphorous atom in the phosphine moiety is low. It is effective to use a metal complex having this pyrazine derivative as a ligand as a catalyst for a reaction in which this feature is exploited.
Although an asymmetric hydrogenation reaction from β-dehydroamino acid to β-amino acid using a rhodium catalyst is widely known in general, catalysts that have high asymmetric induction ability and catalytic activity on both E and Z forms of β-dehydroamino acids, other than catalysts using 1,2-bis(dialkylphosphino)benzene derivatives and 2,3-bis(dialkylphosphino)pyrazine derivatives, are not known well.